But now San Francisco’s civic boosters have decided they want to add a highly unlikely stop to the tourist itinerary: the Uptown Tenderloin, the ragged, druggy and determinedly dingy domain of the city’s most down and out.

And what is the appeal?

“We offer a kind of grittiness you can’t find much anymore,” said Randy Shaw, a longtime San Francisco housing advocate and a driving force behind the idea of Tenderloin tourism. “And what is grittier than the Tenderloin?”

Indeed, after years of neglect and bitter battles over its gentrification, the Tenderloin remains one of the most stubborn challenges in San Francisco, a city that prides itself on its looks, its way of life and its bold solutions to social ills, whether they involve offering universal health care (the city was the first to do so) or banning plastic bags (ditto).

Photo

Civic boosters are hoping to turn the grit of the Uptown Tenderloin district into an attraction, pointing out its ties to music (the Grateful Dead recorded there) and its “rich vice history” (alas, the gambling dens and speakeasies are gone). Credit
Thor Swift for The New York Times

So it is that armed with a recent listing on the National Register of Historic Places, community and city leaders are readying the Tenderloin for its big moment, complete with plans for a new museum, an arts district and walking tours of “the world’s largest collection of historic single-room occupancy hotels.” And unlike, say, the Tenement Museum in New York, which offers tours of a long-unused Lower East Side apartment building, a trip to the Tenderloin could go a step further.

“We can bring people into an SRO and show them where people are living now,” Mr. Shaw said, referring to the single-room occupancy dwellings, or residential hotels, in the area. “And that’s a real plus.”

Mr. Shaw’s plan has the backing of Mayor Gavin Newsom, who announced a city grant last month to help promote “a positive identity for the Tenderloin” and to draw tourism to the area, in part by posting hundreds of plaques on buildings throughout the neighborhood “to create great visual interest for those walking down the community’s streets.”

And oh, what streets those are. Wedged between tourist-friendly Union Square and its liberal-friendly City Hall, the Tenderloin is one of the mostly densely populated areas west of the Mississippi, officials say, with some 30,000 people in 60 square blocks, almost all of which have at least one residential hotel. The district’s drug trade is so widespread, and so wide open, that the police recently asked for special powers to disperse crowds on certain streets. Deranged residents are a constant presence, and after dark the neighborhood can seem downright sinister, with drunken people collapsed on streets and others furtively smoking pipes in doorways.

Photo

Boosters of the Uptown Tenderloin plan tours of one of the many residential hotels, like the Alexander Residence, where Anthony Hack recently relaxed in the lobby.Credit
Thor Swift for The New York Times

All of which, Tenderloin fans contend, is as much a part of San Francisco as flashier, decidedly less seedy attractions like Chinatown or Coit Tower.

“I think a lot of San Franciscans appreciate the Tenderloin,” said Don S. Falk, the executive director of the Tenderloin Neighborhood Development Corporation, a nonprofit group that has renovated and operates 15 residential hotels in the Tenderloin. “It’s part of their identity.”

Encouraging adventure-seeking San Franciscans to visit may be easier than selling the Tenderloin to tourists, city tourism officials say. Laurie Armstrong, a spokeswoman for the San Francisco Convention and Visitors Bureau, called the recent efforts “a step in the right direction,” but added that it was a “very, very long road” to make the neighborhood appealing.

“At this point in time, there aren’t many reasons for visitors to go there,” Ms. Armstrong said. “We don’t really point people away from there, but our job is to point people to things that they can do. And there’s so many things to do in San Francisco.”

Photo

A street in the Uptown Tenderloin district.Credit
Thor Swift for The New York Times

But Mr. Shaw begs to differ, saying the area is chockablock with historical nuggets, like the Hotel Drake, where Frank Capra lived as a starving young director in the early 1920s, or the Cadillac Hotel, built a year after the great 1906 earthquake and fire and where Muhammad Ali later trained. Jerry Garcia also lived at the Cadillac, and he and the Grateful Dead recorded several albums in the area at what is now Hyde Street Studios, as did other Bay Area bands like Creedence Clearwater Revival and Jefferson Airplane.

“And when Miles Davis came to town,” Mr. Shaw said, “he played in the Tenderloin.”

Mr. Shaw, who plans to open a $3 million museum in the Cadillac, believes that baby boomer music fans — and particularly baby boomer Deadheads — will be a core demographic for the Tenderloin, as well as those interested in the neighborhood’s “rich vice history,” which includes gambling dens, speakeasies and pornographic-movie houses.

Experts agree that the neighborhood has historical value, in part because its entrenched poverty and the city’s own prohibitive zoning have prevented development.

“Money sometimes is the enemy of historic preservation,” said Jay Correia, a historian with the California Office of Historic Preservation, which recommended the Tenderloin to the national register. “The irony is because the Tenderloin was economically disadvantaged, there were no funds to modernize.”

Photo

The Uptown Tenderloin is not a regular guidebook highlight.Credit
The New York Times

And while battles over maintaining low-income housing derailed some past efforts to develop the neighborhood, even Mr. Falk, of the nonprofit housing development corporation, says a little new development would not be a bad thing.

“In 1981, gentrification was the most important issue; in 2010, quality of life is the most important issue,” Mr. Falk said. “People with disposable income help local businesses be successful, and those local businesses help support homeless people.”

In addition to tourism — visitors spent nearly $8 billion in San Francisco in 2009 — city officials are also trying more traditional approaches, including applying for a $250,000 grant from the National Endowment for the Arts for public art on the neighborhood’s western border and backing a proposed 250,000-square-foot retail project on its eastern flank.

Mr. Shaw hopes to break ground on his museum by next year and will start posting promotional placards — inviting visitors to “walk, dine, enjoy” the Uptown Tenderloin — this summer. And more plaques are to be mounted on more buildings soon.

Whether posters and plaques are enough to conquer poverty remains to be seen. Chris Patnode, a ruddy-faced self-described wanderer who is staying in a local SRO, said he liked the idea of Tenderloin tourism and seemed to be willing to welcome outsiders. Just as long, of course, as they know when to come knocking.

“In daylight, it’d be O.K.,” said Mr. Patnode, 48. “But people aren’t going to want to come down here at night. I don’t even want to be here at night. And I’m staying here.”

A version of this article appears in print on April 12, 2010, on page A12 of the New York edition with the headline: San Francisco Detours Into Reality Tourism. Order Reprints|Today's Paper|Subscribe